Methods and compositions for bonding silicone polymers to hair and nails

Abstract

Methods for covalently binding a silicone polymer to hair or nails using UV light, a catalyst, a reactive solution, and compositions related thereto. The methods can include synthesizing a photo-reactive silicone and bonding the photo-reactive silicone polymer to hair, nails, or keratin. The methods can also include applying a vinyl-containing silicone polymer and a catalyst, or an aldehyde functionalized silicone polymer and reactive composition, to covalently bond the silicone polymer to hair, nails, or keratin. An advantage of covalently bonding silicone polymer to hair or nails can be that the silicone polymer add strengthens and shine to hair and nails, but are more resistant to washings with soap and shampoo than non-covalently bound silicone polymers.

What is claimed is: 
     
         1 . A method of covalently bonding a silicone polymer to hair, or a nail comprising:
 providing at least one photo-reactive silicone polymer,   bringing the at least one photo-reactive silicone polymer into contact with the hair or the nail, and   applying UV light from a light source to the at least one photo-reactive silicone polymer in the presence of the hair or the nail to produce a covalent bond between at least one silicone polymer and the hair or the nail,   wherein the UV light has a wavelength of from about 200 nm to about 400 nm.   
     
     
         2 . The method of  claim 1 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 250 g/mol to about 50,000 g/mol, and contains from about 5 to about 15 mole percent of a photo-reactive group. 
     
     
         3 . The method of  claim 2 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 4,000 g/mol to about 9,000 g/mol, contains from about 6 to about 7 mole percent of the photo-reactive group, and the photo-reactive group is represented by Formula (I): 
       
         
           
           
               
               
           
         
         wherein the R 1  represents a silicone polymer, and X represents a linking group of a covalent bond or an alkyl group (CH 2 ) 1-10 . 
       
     
     
         4 . The method of  claim 3 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 4,000 g/mol to about 6,000 g/mol, and the silicone polymer is a poly(dimethyl siloxane), and the photo-reactive group is represented by Formula (II): 
       
         
           
           
               
               
           
         
         wherein R 2  represents the poly(dimethyl siloxane) and X represents a linking group of a covalent bond or an alkyl group (CH 2 ) 1-10 . 
       
     
     
         5 . The method of  claim 1 , wherein the bringing step comprises:
 applying the at least one photo-reactive silicone polymer in a solution to the hair or the nail,   wherein the solution comprises an aprotic solvent.   
     
     
         6 . The method of  claim 1 , wherein the providing step comprises:
 synthesizing a compound represented by Formula (I) by reacting a compound represented by Formula (III):   
       
         
           
           
               
               
           
         
         with an amine group attached to a silicone polymer to produce the compound represented by Formula (I) 
       
       
         
           
           
               
               
           
         
         wherein R 1  represents a silicone polymer and L represents a leaving group. 
       
     
     
         7 . The method of  claim 6 , wherein the leaving group is chloride. 
     
     
         8 . The method of  claim 7 , wherein the synthesizing step comprises reacting a benzoyl benzoic acid with thionyl chloride or oxalyl chloride to produce the compound of Formula (III). 
     
     
         9 . The method of  claim 1 , wherein, before or after the bringing step, the hair is subject to a permanent coloration, demi-permanent coloration, semi-permanent coloration, temporary hair color, or a straightening treatment or combination thereof. 
     
     
         10 . A method of treating a hair to prevent or mitigate effects of dryness, or flatness, and/or preventing color bleeding in a hair comprising:
 applying a composition comprising at least one photo-reactive silicone polymer to the hair.   
     
     
         11 . The method of  claim 10 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 250 g/mol to about 50,000 g/mol, and contains from about 5 to about 15 mole percent of a photo-reactive group. 
     
     
         12 . The method of  claim 11 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 4,000 g/mol to about 9,000 g/mol, contains from about 6 to about 7 mole percent of the photo-reactive group, and the photo-reactive group is represented by Formula (I): 
       
         
           
           
               
               
           
         
         wherein the R 1  represents a silicone polymer. 
       
     
     
         13 . The method of  claim 10 , wherein the composition comprises:
 the at least one photo-reactive silicone polymer, wherein the composition comprises an aprotic solvent.   
     
     
         14 . A method of covalently bonding a silicone polymer to hair, or a nail comprising:
 providing at least one photo-reactive silicone polymer,   bringing the at least one photo-reactive silicone polymer into contact with the hair or the nail, and   applying UV light from a light source to the at least one photo-reactive silicone polymer in the presence of the hair or the nail to produce a covalent bond between at least one silicone polymer and the hair or the nail,   wherein the UV light has a wavelength of from about 200 nm to about 400 nm,   wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 250 g/mol to about 50,000 g/mol, and contains from about 5 to about 15 mole percent of a photo-reactive group,   wherein the photo-reactive group is represented by Formula (V):   
       
         
           
           
               
               
           
         
         R 4  is selected from a (C 1 -C 10 ) hydrocarbyl group; 
         R 5  is selected from the group consisting of: —N—(C═S)—N—; —(N—H)—; and —N═S(—H)—N—; —(C═O)—O—; —O—(C═O)—; and a (C 1 -C 6 ) hydrocarbyl group, wherein the hydrocarbyl group is optionally substituted with one or more oxygen atoms, or hydroxyl groups; and 
         R 6  represents the silicone polymer; and 
         Y represents a linking group of a covalent bond or an alkyl group (CH 2 ) 1-10 . 
       
     
     
         15 . A method of bonding a silicone polymer to hair, or a nail comprising:
 providing at least one photo-reactive silicone polymer,   bringing the at least one photo-reactive silicone polymer into contact with the hair or the nail, and   applying UV light from a light source to the at least one photo-reactive silicone polymer in the presence of the hair or the nail to bond at least one silicone polymer to the hair or the nail,   wherein the UV light has a wavelength of from about 200 nm to about 400 nm.   
     
     
         16 . The method of  claim 15 , wherein the providing step comprises reacting a compound a benzoyl benzoic acid with a silicone polymer having at least one amine group to form a photo-reactive silicone polymer. 
     
     
         17 . The method of  claim 15 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 250 g/mol to about 75,000 g/mol, and contains from about 0.5 to about 50 mole percent of a photo-reactive group. 
     
     
         18 . The method of  claim 17 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 4,000 g/mol to about 60,000 g/mol, contains from about 1 to about 15 mole percent of the photo-reactive group, and the photo-reactive group is represented by Formula (I): 
       
         
           
           
               
               
           
         
         wherein the R 1  represents a silicone polymer, and X represents a linking group selected from the group consisting of: a covalent bond and a (C 1 -C 10 ) hydrocarbyl group, optionally substituted with one or more of oxygen, nitrogen, sulfur, or silicon. 
       
     
     
         19 . The method of  claim 18 , wherein the at least one photo-reactive silicone polymer has a molecular weight of from about 4,000 g/mol to about 50,000 g/mol, and the silicone polymer is a poly(dimethyl siloxane), and the photo-reactive group is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein R 2  represents the poly(dimethyl siloxane), and X represents a linking group selected from the group consisting of: a covalent bond and a (C 1 -C 10 ) hydrocarbyl group, optionally substituted with one or more of oxygen, nitrogen, sulfur, or silicon. 
       
     
     
         20 . The method of  claim 15 , wherein the bringing step comprises:
 applying the at least one photo-reactive silicone polymer in a solution to the hair or the nail.   
     
     
         21 . The method of  claim 15 , wherein the solution comprises an aprotic solvent. 
     
     
         22 . The method of  claim 15 , wherein the providing step comprises:
 reacting a compound represented by Formula (III):   
       
         
           
           
               
               
           
         
         to produce the compound represented by Formula (I) 
       
       
         
           
           
               
               
           
         
         wherein R 1  represents a silicone polymer; X represents a linking group selected from the group consisting of: a covalent bond and a (C 1 -C 10 ) hydrocarbyl group, optionally substituted with one or more of oxygen, nitrogen, sulfur, or silicon; and L represents Br or Cl. 
       
     
     
         23 . The method of  claim 15 , further comprising a step of synthesizing a compound of Formula (III) by reacting a benzoyl benzoic acid with thionyl chloride, oxalyl chloride, or phosphorous tribromide to produce the compound of Formula (III). 
     
     
         24 . The method of  claim 15 , wherein the providing step comprises:
 reacting a compound of Formula (Ma);   
       
         
           
           
               
               
           
         
       
       to form a compound of Formula (I); 
       
         
           
           
               
               
           
         
         wherein R 1  represents a silicone polymer; and X represents a linking group selected from the group consisting of: a covalent bond and a (C 1 -C 10 ) hydrocarbyl group, optionally substituted with one or more of oxygen, nitrogen, sulfur, or silicon. 
       
     
     
         25 . The method of  claim 15 , wherein, before or after the bringing step, the hair is subject to a permanent coloration, demi-permanent coloration, semi-permanent coloration, temporary hair color, or a straightening treatment or combination thereof. 
     
     
         26 . A method of bonding a silicone polymer to hair, or a nail comprising:
 providing at least one photo-reactive silicone polymer,   bringing the at least one photo-reactive silicone polymer into contact with the hair or the nail, and   applying UV light from a light source to the at least one photo-reactive silicone polymer in the presence of the hair or the nail to bond at least one silicone polymer to the hair or the nail,   wherein the UV light has a wavelength of from about 200 nm to about 400 nm.   
     
     
         27 . A method of applying a photo-reactive silicone polymer to hair or a nail comprising:
 providing at least one photo-reactive silicone polymer, and   bringing the at least one photo-reactive silicone polymer into contact with the hair or the nail,   wherein the photo-reactive silicone polymer is capable of bonding to hair or a nail when the photo-reactive silicone polymer is exposed to UV light having a wavelength of from about 200 nm to about 400 nm from about 1 s to about 4 hours.